10 Reasons Woodstock is the Midwestern Stars Hollow

Gilmore Girls: A Year in the Life arrived on Netflix Streaming last week and people are losing their minds over it. I have been purposely avoiding ANY mention of it on social media because it’s been a while since I saw the show so I’m busy re-watching the first seven seasons before I move on to the new episodes. I’m up to season 7 so it won’t be too much longer!

Why is Gilmore Girls such a great show? There are lots of reason, but one of the best things about Gilmore Girls is, of course, Stars Hollow.

Sadly, it’s a fictional town made up for the show, constructed on a Warner Bros. lot in California. I mean, someplace as awesome as Stars Hollow can’t really be real anyway. Or can it?

Believe it or not, you can find a pretty amazing Stars Hollow substitute right here in the Midwest. I would even go so far as saying that it is BETTER than Stars Hollow (I may be slightly biased since I live in Woodstock, but check out the list below and I think you’ll agree). If you just can’t get enough of Gilmore Girls and Stars Hollow, I strongly suggest you get a babysitter for the kids, grab a girl friend, and head out for a lovely day of shopping and meandering in Woodstock, Illinois.

How is Woodstock the Stars Hollow of the Midwest? I’ll give you ten reasons:

#1: Town square with a gazebo

I think the town square is one of the most filmed “characters” in the show. It’s in the opening sequence, Rory and Lorelei pass it at least once in nearly every show, and it’s often the center of town events.
Woodstock has a historic square, complete with gazebo, with green grass and bright flowers in the summer, colorful leaves in the fall, and covered in sparkly snow in the winter.

#2: History

The legend of the star-crossed lovers, “Sores and Boils Alley”, and the battle with the Redcoats are just a few of the historic Stars Hollow events referenced in the Gilmore Girls. Woodstock’s history might not go back quite as far, but we’ve got history, too:

Eugene V. Debs served a short federal prison sentence in Woodstock in 1895 after the Pullman labor strike in Chicago.

Woodstock was known as “Typewriter City” because there where two typewriter factories and by the 1920s more than half of the country’s typewriters were manufactured in Woodstock.

Historic buildings galore – the Old McHenry County Courthouse and jail (now site of art galleries and a restaurant) and the Opera House, just to name a couple. If you’re interested in local history, there is a fantastic Historic Downtown Walking Tour Guide.

Orson Welles spent years in Woodstock as a young man, first performed in Woodstock, and debuted as a professional theatre director at the Woodstock Opera House.

Just some of Woodstock’s famous residents: Chester Gould (creator of the Dick Tracy comic strip), Emma Goldman (political activist), and actress Jessica Biel.

#3: Tourism

Tourism is important in Stars Hollow, and it’s equally important in Woodstock. Tourists are drawn to Woodstock for many reasons, but one is that they’ve seen it before. If Woodstock looks a little familiar to you it’s probably not just the resemblance to Stars Hollow; you may have see it before when it played Punxsutawney in Groundhog Day and it made a short appearance in Planes, Trains, and Automobiles. On the small screen, Woodstock’s own Angelo’s Family Restaurant appeared on Robert Irvine’s Restaurant: Impossible: It’s All Greek to Me. (Note: While the restaurant is still open here on the Square, it’s changed hands since the show and is now Papa G’s.)

People are drawn to Woodstock year-round, but especially in February for the Groundhog Day festivities which last about a week. The annual schedule includes the “Awakening of the Groundhog”, free showings of the Groundhog Day movie, a dinner dance, Family Funday, walking tours of the filming sites, and lots more. Best of all, many of the events and activities are free. For a full schedule, check out WoodstockGroundhogDay.org.

#4: Proximity to a big city

Stars Hollow has New York, Woodstock has Chicago. It’s not exactly clear from Gilmore Girls how far New York is from Stars Hollow; it’s not close, but it’s close enough that Lorelai, Sookie, Rory, Paris, and Paris’s friends can drive there for a Bangles concert, and Rory can hop on a bus to go visit Jess in the city during school hours.

Woodstock is 60 miles northwest of Chicago. It’s an easy drive on the expressway or you can hop on Metra’s Union Pacific/Northwest Line which will take you directly from Chicago’s Ogilvie Station to Woodstock.

#5: Community events

Stars Hollow has a pretty tight-knit community; many residents know each other and they regularly come together to participate in area activities and events, like the Firelight Festival, Movie Night in the Square, the Spring Fling, the Winter Festival. It seems like there’s always something going on in Stars Hollow.

Woodstock has some community events too, including a farmers’ market on the Square on Tuesdays and Saturdays May through October, the above-mentioned Groundhog Day festivities, Movies in the Park (and not just The Yearling!), Fair Diddley Craft Show, band concerts every Wednesday throughout the summer, Harvest Fest, the Woodstock Folk Festival, Jazz on the Square Festival, and the Lighting of the Square. Santa’s hut appears on the Square in November and he sees kids during select hours until Christmas, and there are even free horse-drawn carriage rides around the Square on certain nights during November and December.

#6: The Inn

The Independence Inn in Gilmore Girls is pretty cool, but not nearly as cool as Lorelai and Sookie’s Dragonfly Inn. Seriously – I want to stay there. We don’t have a Dragonfly Inn in Woodstock, but there are a couple Bed & Breakfast places here – Royal Victorian Manor (which was The Cherry Street Inn in Groundhog Day) and the Bundling Board Inn.

#7: Antiques

Stars Hollow has Kim’s Antiques and, presumably, other antique stores since Emily Gilmore talks about antiquing in Stars Hollow. In Woodstock if you want antiques you have to check out the Colonial Antique Mall with 35,000 square feet of antiques from multiple dealers.

#8: Shopping

Rory and Lorelai love to shop – who doesn’t? Forget the chain stores because Stars Hollow AND Woodstock both have some amazing local shops. For comparison:

Stars Hollow

Woodstock, IL

Luke's Diner

Papa G's, Three Brothers, or Public House

Stars Hollow Books

Read Between the Lynes

Black, White, & Read Bookshop & Theater

Classic Cinemas

Stars Hollow Beauty Supply

Burseth Farm (handmade soap)

Sophie's Music

Dave's Woodstock Music

It doesn’t stop there. Some other amazing local shops to check out in Woodstock:

Sparrow’s Nest Thrift Store

The Backdrop

The Thoughtfulness Shop

Expressly Leslie (vegetarian restaurant)

Stage Left Cafe

Mixin Mingle (party and event venue)

Green Box Boutique

Down 2 Earth

Sewing Concepts

Sonshine Girl Boutique

Diva’s Attic

Material Things

#9: Great people

Stars Hollow wouldn’t be Stars Hollow without Rory, Lorelai, Luke, Miss Patty, Kirk, Taylor… the list goes on. Woodstock doesn’t have anyone quite as crazy and quirky as Kirk and Taylor, at least not that I’ve met yet, but the people are friendly and amazing. Until you visit you’ll just have to trust me.

#10: Coffee

I saved the most important for last. Gilmore Girls wouldn’t be Gilmore Girls without coffee. Sadly, there’s no Luke’s in Woodstock. However, there is an Ethereal Confections. Cozy atmosphere, yummy coffee (I hear; I’m not a coffee drinker, but I can vouch for the hot tea and hot cocoa!), and something Luke’s doesn’t have – artisan chocolate. They serve just about every beverage you can imagine (alcohol included), plus panini, soup, small plates, breakfast items, cheese plates, and desserts to die for. YUM. There’s comfy seating, art on the walls, and the whole place smells like chocolate. Can you imagine a better place to be?